Mayoral candidate Rudolph Giuliani greets voters at a New York City parade in August 1989. Giuliani narrowly lost that year's election to Democrat David Dinkins. He defeated Dinkins four years later.
Michael Hirsch/Newsmakers/Getty Images
hide caption

toggle caption

Michael Hirsch/Newsmakers/Getty Images

Mayoral candidate Rudolph Giuliani greets voters at a New York City parade in August 1989. Giuliani narrowly lost that year's election to Democrat David Dinkins. He defeated Dinkins four years later.

Michael Hirsch/Newsmakers/Getty Images

Giuliani Profile

Read about Rudolph Giuliani’s political career and his prospects as a presidential candidate:

Some first-time candidates struggle just for name recognition. Not Rudolph Giuliani. In 1989, he had just resigned as United States Attorney for southern New York. For years, he had prosecuted mob bosses, shady Wall Street investors and corrupt politicians. He had gone after big names — and become one himself. But the transition from prosecutor to candidate didn't come easily, says his then-campaign manager, Peter Powers.

"Frankly, Rudy was not comfortable as a candidate in the beginning," Powers says. "He'd sheepishly wave to a crowd. He didn't have that big politician wave. He was shy. He looked uncomfortable at times."

Giuliani asked Powers to take over his campaign when he was way behind in the polls, even though Powers had no professional political experience. What Powers did have was Giuliani experience. The two had been best friends since attending Bishop Loughlin High School in Brooklyn. They ran their first campaigns together at Manhattan College, though back then it was Giuliani managing Powers' campaign for senior class president.

"We lost," Powers says. "And midway through 1989, when he made me his campaign manager, I could see he was starting to worry that I was going to get even."

In 1989, Giuliani vowed to rid the city of "crime, crack and corruption," as he put it. He cast himself as a moderate, running on both the Republican and Liberal party tickets. Giuliani often compared himself to New York's famous reformist mayor of the 1930s, Fiorello La Guardia. He pointed out that La Guardia, like himself a Republican, had also run with the support of Democrats and other parties.

But the campaign did not go as he had planned. Giuliani expected to run against three-term incumbent mayor Ed Koch, who had alienated many liberals and minorities. But Koch lost the Democratic primary to Manhattan Borough President David Dinkins, an experienced African-American politician, who was known for his courtly demeanor. It changed everything for Giuliani.

"He was now standing, in a sense, in the way of history, that is, the election of the first black mayor in the city of New York," says Doug Muzzio, a former Dinkins campaign worker who is now a professor at the City University of New York.

Muzzio says the Giuliani campaign never quite got its footing after that. They "jettisoned this progressive liberal campaign and really went on the negative," he adds.

Giuliani attacked Dinkins' honesty, citing a questionable transfer of stock to his son, and his failure, nearly two decades earlier, to pay his taxes for several years. Giuliani also tagged Dinkins as a "Jesse Jackson Democrat." That was an appeal to the city's large contingent of Jewish voters, who had despised Jackson ever since he used an anti-Semitic epithet to describe New York City. In this context, Giuliani's signature issue of crime took on racial overtones, says political consultant Norman Adler.

"A lot of people wanted to see a mayor who would do something about crime," Adler says. "But ... most of this was blamed on minorities and so the imputation was that if you wanted to see things continue, just go ahead and elect a black man."

"It was a campaign where if you attacked David Dinkins, people would say you were being a racist," Powers says. "That to me is totally unfair. Because I think its racist to say you can't attack someone because they're black the same way you would attack them if they're white."

On issues other than crime, Giuliani was still getting his footing. For example, he was against abortion rights — at first. But over the course of the campaign he changed his position, becoming pro-choice like the vast majority of New Yorkers. He even supported public funding of abortions for poor women. An analysis of the '89 campaign done by Giuliani's own staffers called his handling of the abortion issue one of his greatest missteps.

Lessons in Defeat

Yet in the end, Giuliani came pretty close to winning the election. In a predominately Democratic city, Giuliani only lost by 50,000 votes. Bill Lynch, Dinkins' campaign manager, thinks many people were uncomfortable voting for an African American for mayor.

"In previous campaigns, when someone won the Democratic primary, that was paramount to winning the election," Lynch notes. "It was supposed to be a cakewalk. That was not the case for Mayor Dinkins."

"We learned a lot from it," says Powers, who believes that, in the long run, losing turned out to be a good thing.

"It showed the character of the man, a person who learned from defeat ... and came back the next time and was successful," Powers adds.

In the 1993 rematch, Giuliani beat Dinkins by roughly the same small number of votes he had lost by four years earlier. City University professor Doug Muzzio says that in the interval, Giuliani become a better campaigner. But his approach to the issues didn't change much.

"He is flexible ideologically," Muzzio says. "He will in one sense flip flop or in a more or less negative sense, nuance the question. And you can see that with his gun-control stand, his abortion stand."

For example, Giuliani still supports abortion rights, but he now also advocates appointing strict constructionist judges likely to overturn them. And he was in favor of gun control when he was mayor, but now says that what's right for New York City may not apply to other parts of the country.

"This is a guy who sees himself as the protector of people against invidious forces," Adler says, "whether crack dealers, terrorists, or thugs in housing projects. And that's the way he's always going to interpret things."

Right now, it's working for him, as the country still comes to grips with the attacks six years ago on the Pentagon and Giuliani's New York.